Sodium hydride → 1-Fluoro-2-fluoromethyl-3-butyn-2-yl methanesulfonate

An amount (1.2 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol was dissolved in tetrahydrofuran (10 ml); to the solution under cooling with ice, 60% oily sodium hydride (0.48 g) was added under a nitrogen atmosphere. The solution was stirred for 30 minutes under cooling with ice and then methanesulfonyl chloride (1.1 ml) was added dropwise. The solution was stirred for 2.5 hours while its temperature was raised to room temperature. To the reaction mixture, etcher was added, followed by extraction with diethyl ether. The extract was washed with water and a saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; 30% ethyl acetate/hexane) to give the titled compound (1.6 g).

1. additionwas added under a nitrogen atmosphere
2. temperatureunder cooling with ice
3. stirringThe solution was stirred for 2.5 hours while its temperature
4. additionTo the reaction mixture, etcher was added
5. extractionfollowed by extraction with diethyl ether
6. washThe extract was washed with water
7. dry with materiala saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-02b566c70a9d4d62af851036f3ec990d

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455708B1